C₁₈ Dibenzocyclooctadiene Lignans from Kadsura philippinensis
Four new C18 dibenzocyclooctadiene lignans, kadsuphilins A (1) and B (3), 6-epi-gomisin (2), and 1-demethylkadsuphilin A (4), along with eight known related metabolites, were isolated from an EtOAc fraction of an alcoholic extract of the aerial parts of Kadsura philippinensis growing in Taiwan. The...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-06, Vol.69 (6), p.963-966 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Shen, Y.C Liaw, C.C Cheng, Y.B Ahmed, A.F Lai, M.C Liou, S.S Wu, T.S Kuo, Y.H Lin, Y.C |
| description | Four new C18 dibenzocyclooctadiene lignans, kadsuphilins A (1) and B (3), 6-epi-gomisin (2), and 1-demethylkadsuphilin A (4), along with eight known related metabolites, were isolated from an EtOAc fraction of an alcoholic extract of the aerial parts of Kadsura philippinensis growing in Taiwan. The structures of 1-4 were elucidated on the basis of spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The configurations of the biphenyl and cyclooctadiene moieties were deduced from circular dichroism (CD) and NOESY NMR spectra, respectively. Some of the compounds showed radical-scavenging activity in a DPPH-HPLC method. |
| doi_str_mv | 10.1021/np058134j |
| format | Article |
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The structures of 1-4 were elucidated on the basis of spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The configurations of the biphenyl and cyclooctadiene moieties were deduced from circular dichroism (CD) and NOESY NMR spectra, respectively. Some of the compounds showed radical-scavenging activity in a DPPH-HPLC method.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np058134j</identifier><identifier>PMID: 16792420</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>anticarcinogenic activity ; antioxidant activity ; Biological and medical sciences ; Biphenyl Compounds ; chemical structure ; cultured cells ; Cyclooctanes - chemistry ; Cyclooctanes - isolation & purification ; Cyclooctanes - pharmacology ; cytotoxicity ; demethylkadsuphilin ; dibenzocyclooctadiene lignan ; free radical scavengers ; Free Radical Scavengers - chemistry ; Free Radical Scavengers - isolation & purification ; Free Radical Scavengers - pharmacology ; General pharmacology ; gomisin ; humans ; kadsuphilins ; Kadsura ; Kadsura - chemistry ; Kadsura philippinensis ; lignans ; Lignans - chemistry ; Lignans - isolation & purification ; Lignans - pharmacology ; Medical sciences ; medicinal plants ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Oriental traditional medicine ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; Picrates - pharmacology ; Plants, Medicinal - chemistry ; Schisandraceae ; spectral analysis ; Taiwan</subject><ispartof>Journal of natural products (Washington, D.C.), 2006-06, Vol.69 (6), p.963-966</ispartof><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17899170$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16792420$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shen, Y.C</creatorcontrib><creatorcontrib>Liaw, C.C</creatorcontrib><creatorcontrib>Cheng, Y.B</creatorcontrib><creatorcontrib>Ahmed, A.F</creatorcontrib><creatorcontrib>Lai, M.C</creatorcontrib><creatorcontrib>Liou, S.S</creatorcontrib><creatorcontrib>Wu, T.S</creatorcontrib><creatorcontrib>Kuo, Y.H</creatorcontrib><creatorcontrib>Lin, Y.C</creatorcontrib><title>C₁₈ Dibenzocyclooctadiene Lignans from Kadsura philippinensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Four new C18 dibenzocyclooctadiene lignans, kadsuphilins A (1) and B (3), 6-epi-gomisin (2), and 1-demethylkadsuphilin A (4), along with eight known related metabolites, were isolated from an EtOAc fraction of an alcoholic extract of the aerial parts of Kadsura philippinensis growing in Taiwan. The structures of 1-4 were elucidated on the basis of spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The configurations of the biphenyl and cyclooctadiene moieties were deduced from circular dichroism (CD) and NOESY NMR spectra, respectively. Some of the compounds showed radical-scavenging activity in a DPPH-HPLC method.</description><subject>anticarcinogenic activity</subject><subject>antioxidant activity</subject><subject>Biological and medical sciences</subject><subject>Biphenyl Compounds</subject><subject>chemical structure</subject><subject>cultured cells</subject><subject>Cyclooctanes - chemistry</subject><subject>Cyclooctanes - isolation & purification</subject><subject>Cyclooctanes - pharmacology</subject><subject>cytotoxicity</subject><subject>demethylkadsuphilin</subject><subject>dibenzocyclooctadiene lignan</subject><subject>free radical scavengers</subject><subject>Free Radical Scavengers - chemistry</subject><subject>Free Radical Scavengers - isolation & purification</subject><subject>Free Radical Scavengers - pharmacology</subject><subject>General pharmacology</subject><subject>gomisin</subject><subject>humans</subject><subject>kadsuphilins</subject><subject>Kadsura</subject><subject>Kadsura - chemistry</subject><subject>Kadsura philippinensis</subject><subject>lignans</subject><subject>Lignans - chemistry</subject><subject>Lignans - isolation & purification</subject><subject>Lignans - pharmacology</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Oriental traditional medicine</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>Picrates - pharmacology</subject><subject>Plants, Medicinal - chemistry</subject><subject>Schisandraceae</subject><subject>spectral analysis</subject><subject>Taiwan</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFz81u1DAUBWALgehQWPACkA3sAvf6-ideVgMU1FFBtBVLy3ac4pJx0nhGouzoiufskxA0A6zO4nw60mHsKcIrBI6v8wiyQRJX99gCJYdaAZf32QJQUU2NEgfsUSlXAEBg5EN2gEobLjgs2NHy7vbn3e2v6k3yMf8Ywk3ohyFsXJtijtUqXWaXS9VNw7o6cW3ZTq4av6Y-jWPKMZdUHrMHnetLfLLPQ3bx7u358n29-nj8YXm0qjuOalNzLjUKTyRUiMoraRrvDQWCFqJphaaOvPY6yojKkQvBgBetkIRRtArpkL3c7Y7TcL2NZWPXqYTY9y7HYVusaqTmoMUMn-3h1q9ja8cprd10Y_-ensGLPXAluL6bXA6p_He6MQb1H1fvXCqb-P1f76ZvVmnS0p5_OrMnp80pP6bP9svsn-985wbrLqd58-KMAxIg4hyGfgNM_n5v</recordid><startdate>200606</startdate><enddate>200606</enddate><creator>Shen, Y.C</creator><creator>Liaw, C.C</creator><creator>Cheng, Y.B</creator><creator>Ahmed, A.F</creator><creator>Lai, M.C</creator><creator>Liou, S.S</creator><creator>Wu, T.S</creator><creator>Kuo, Y.H</creator><creator>Lin, Y.C</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>200606</creationdate><title>C₁₈ Dibenzocyclooctadiene Lignans from Kadsura philippinensis</title><author>Shen, Y.C ; Liaw, C.C ; Cheng, Y.B ; Ahmed, A.F ; Lai, M.C ; Liou, S.S ; Wu, T.S ; Kuo, Y.H ; Lin, Y.C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f216t-225714b3346ce6b6598bb93c30d0e9d473f3b7b7e5e16a3acc90b4d4531e4d613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>anticarcinogenic activity</topic><topic>antioxidant activity</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds</topic><topic>chemical structure</topic><topic>cultured cells</topic><topic>Cyclooctanes - chemistry</topic><topic>Cyclooctanes - isolation & purification</topic><topic>Cyclooctanes - pharmacology</topic><topic>cytotoxicity</topic><topic>demethylkadsuphilin</topic><topic>dibenzocyclooctadiene lignan</topic><topic>free radical scavengers</topic><topic>Free Radical Scavengers - chemistry</topic><topic>Free Radical Scavengers - isolation & purification</topic><topic>Free Radical Scavengers - pharmacology</topic><topic>General pharmacology</topic><topic>gomisin</topic><topic>humans</topic><topic>kadsuphilins</topic><topic>Kadsura</topic><topic>Kadsura - chemistry</topic><topic>Kadsura philippinensis</topic><topic>lignans</topic><topic>Lignans - chemistry</topic><topic>Lignans - isolation & purification</topic><topic>Lignans - pharmacology</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Oriental traditional medicine</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>Picrates - pharmacology</topic><topic>Plants, Medicinal - chemistry</topic><topic>Schisandraceae</topic><topic>spectral analysis</topic><topic>Taiwan</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shen, Y.C</creatorcontrib><creatorcontrib>Liaw, C.C</creatorcontrib><creatorcontrib>Cheng, Y.B</creatorcontrib><creatorcontrib>Ahmed, A.F</creatorcontrib><creatorcontrib>Lai, M.C</creatorcontrib><creatorcontrib>Liou, S.S</creatorcontrib><creatorcontrib>Wu, T.S</creatorcontrib><creatorcontrib>Kuo, Y.H</creatorcontrib><creatorcontrib>Lin, Y.C</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shen, Y.C</au><au>Liaw, C.C</au><au>Cheng, Y.B</au><au>Ahmed, A.F</au><au>Lai, M.C</au><au>Liou, S.S</au><au>Wu, T.S</au><au>Kuo, Y.H</au><au>Lin, Y.C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>C₁₈ Dibenzocyclooctadiene Lignans from Kadsura philippinensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2006-06</date><risdate>2006</risdate><volume>69</volume><issue>6</issue><spage>963</spage><epage>966</epage><pages>963-966</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Four new C18 dibenzocyclooctadiene lignans, kadsuphilins A (1) and B (3), 6-epi-gomisin (2), and 1-demethylkadsuphilin A (4), along with eight known related metabolites, were isolated from an EtOAc fraction of an alcoholic extract of the aerial parts of Kadsura philippinensis growing in Taiwan. The structures of 1-4 were elucidated on the basis of spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The configurations of the biphenyl and cyclooctadiene moieties were deduced from circular dichroism (CD) and NOESY NMR spectra, respectively. Some of the compounds showed radical-scavenging activity in a DPPH-HPLC method.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>16792420</pmid><doi>10.1021/np058134j</doi><tpages>4</tpages></addata></record> |
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| subjects | anticarcinogenic activity antioxidant activity Biological and medical sciences Biphenyl Compounds chemical structure cultured cells Cyclooctanes - chemistry Cyclooctanes - isolation & purification Cyclooctanes - pharmacology cytotoxicity demethylkadsuphilin dibenzocyclooctadiene lignan free radical scavengers Free Radical Scavengers - chemistry Free Radical Scavengers - isolation & purification Free Radical Scavengers - pharmacology General pharmacology gomisin humans kadsuphilins Kadsura Kadsura - chemistry Kadsura philippinensis lignans Lignans - chemistry Lignans - isolation & purification Lignans - pharmacology Medical sciences medicinal plants Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oriental traditional medicine Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals Picrates - pharmacology Plants, Medicinal - chemistry Schisandraceae spectral analysis Taiwan |
| title | C₁₈ Dibenzocyclooctadiene Lignans from Kadsura philippinensis |
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